A novel bridged nucleoside bearing a conformationally switchable sugar moiety in response to redox changes

Baba, Takeshi; Kodama, Tetsuya; Mori, Kazuto; Imanishi, Takeshi; Obika, Satoshi

doi:10.1039/c0cc02484h

Cited by 19 publications

(12 citation statements)

References 29 publications

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“…Thus, SeLNA has the potential to work as a redox switch for various biomolecules. There have been few reports on nucleosides or nucleotides that can reversibly change their structures and properties in response to the surrounding redox conditions 29…”

Section: Methodsmentioning

confidence: 99%

Selenomethylene Locked Nucleic Acid Enables Reversible Hybridization in Response to Redox Changes

et al. 2013

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Locking up selenium: A new conformationally restricted nucleic acid with a 2′,4′‐selenomethylene bridge (SeLNA) can be reversibly converted into its oxidized form (SeOLNA), and the hybridization of a modified oligonucleotide was shown to be dependent on the oxidation state. A SeLNA‐modified molecular‐beacon‐type probe (see scheme; F=fluorophore, Q=quencher) can be used as a sensor for changes in the redox environment.

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Section: Methodsmentioning

confidence: 99%

Selenomethylene Locked Nucleic Acid Enables Reversible Hybridization in Response to Redox Changes

et al. 2013

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“…Disulfide bonds are capable of undergoing reversible formation and scission in response to surrounding redox changes; as a result, a nucleoside analogue containing a disulfide bridge can undergo redox-responsive reversible changes in the conformation of its sugar moiety. 23 We began our synthesis of disulfide-type BNA nucleoside with the known nucleoside derivative 6 (Scheme 6). Triflation of the hydroxy groups followed by an alkali-mediated hydrolysis gave the arabino-type nucleoside 7.…”

Section: ′4′-bridged Nucleic Acid Analogues Bearing External Stimuli-responsive Bridged Moietiesmentioning

confidence: 99%

Development of External Stimuli-Responsive Nucleic Acids by Sugar, Backbone, and Nucleobase Modification

Morihiro

Kodama

Obika

2014

Synlett

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Nucleic acids are the principal materials for the preservation and flow of genetic information. The control of the properties of nucleic acids by using external stimuli is important for regulating biological processes and for the possibility of developing unique molecular machines. This account summarizes the development of external stimuli-responsive nucleic acids by our group. Our external stimuli-responsive nucleic acids are designed and synthesized through sugar, backbone, and nucleobase modifications. Various external stimuli, such as light, acids, or oxidants/reductants can trigger changes in nucleic acid structure. By means of such structural alterations, various properties of nucleic acid, including their hybridization ability, nuclease resistance, backbone degradability, and base-recognition ability, can be changed. 1 Introduction 2 External Stimuli-Responsive Nucleic Acids 2.1 2′,4′-Bridged Nucleic Acid Analogues Bearing External Stimuli-Responsive Bridged Moieties 2.2 Oligonucleotides Containing a P-N Phosphoramidite Linkage for Double-Stranded DNA-Templated Digestion 2.3 Light-Triggered Change in the Hydrogen-Bonding Pattern of a Nucleobase Analogue Enables a Strand-Exchange Reaction 3 Conclusions

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“…We previously synthesized a BNA monomer bearing a disulfide bridged structure (disulfide-type BNA, 1). 22 It was expected that this disulfide-type BNA with a 1,2-dithiane structure would be converted to a BNA bearing a thiol at the 6¢-position by photoirradiation, 23 and various molecules were conjugated at the 6¢-position via the thiol. Since this thiol-containing BNA has the skeleton of 2¢-thio-LNA, which has high duplex-forming ability for complementary RNA and high enzymatic stability, 24 the thiolcontaining BNA was also anticipated to have similar characters in those regards.…”

Section: Design and Synthesis Of Phosphoramidite And Preparation Of O...mentioning

confidence: 99%

“…The thiol-containing BNA was synthesized from disulfidetype BNA monomer 1 22 as shown in Scheme 1. First, the nucleoside 1, reported previously by us, was treated with tertbutyldiphenylsilyl chloride (TBDPSCl) in the presence of N,Ndimethyl-4-aminopyridine to protect the 3¢-and 5¢-hydroxy groups.…”

Section: Design and Synthesis Of Phosphoramidite And Preparation Of O...mentioning

confidence: 99%

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Bridged nucleic acid conjugates at 6′-thiol: synthesis, hybridization properties and nuclease resistances

et al. 2011

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The bridged nucleic acid (BNA) containing a thiol at the 6'-position in the bridged structure was synthesized from the disulfide-type BNA and conjugated with various functional molecules via the thioether or the disulfide linkage post-synthetically and efficiently in solution phase. The disulfide-linked conjugate was cleaved under reductive conditions derived from glutathione and an oligonucleotide bearing a free thiol was released smoothly. Conjugated functional molecules had great effects on duplex stability with the DNA complement. In contrast, the molecules little influenced the stability with the RNA complement. Moreover, the oligonucleotides with functional groups at the 6'-position had as high or higher resistances against 3'-exonuclease than phosphorothioate oligonucleotide (S-oligo).

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A novel bridged nucleoside bearing a conformationally switchable sugar moiety in response to redox changes

Abstract: A novel nucleoside analog with a disulfide bridge structure at the sugar moiety, which shows redox-responsive reversibility of the sugar conformation due to formation and scission of the disulfide bond, was designed and synthesized.

Cited by 19 publications

References 29 publications

Selenomethylene Locked Nucleic Acid Enables Reversible Hybridization in Response to Redox Changes

Selenomethylene Locked Nucleic Acid Enables Reversible Hybridization in Response to Redox Changes

Development of External Stimuli-Responsive Nucleic Acids by Sugar, Backbone, and Nucleobase Modification

Bridged nucleic acid conjugates at 6′-thiol: synthesis, hybridization properties and nuclease resistances

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